I'd replace that 1/2 moon key and see if the pulley will tighten back up using a different nut
Is the keyway in the pulley in good shape? like the damage on the spindle is clear at the top end of the threads and the only way that key could have escaped is if the nut were backed way off to give it room enough to get the hell out of Dodge so to speak. Might want to clean up the threads on the spindle and give it a try.
Good luck!
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